Hydrochloric Acid → 5-Cyclohexyl-2,2-dimethyl-5-(1-hydroxyethyl)-1,3-dioxane

Reaction equation

[CH3:1][Mg]I.[CH:4]1([C:10]2([CH:18]=[O:19])[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[O:12][CH2:11]2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.Cl>CCOCC>[CH:4]1([C:10]2([CH:18]([OH:19])[CH3:1])[CH2:15][O:14][C:13]([CH3:16])([CH3:17])[O:12][CH2:11]2)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

Procedure

Methyl magnesium iodide (3.0 ml, 3M solution in ether) was added to a solution of 5-cyclohexyl-2,2-dimethyl-5- formyl-1,3-dioxane (1.8 g.) in dry ether (50 ml.) The mixture was refluxed, with stirring, for two hours, cooled and poured into a mixture of 2N hydrochloric acid solution in ice. The aqueous mixture was extracted with ether. The ether extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. 5-Cyclohexyl-2,2-dimethyl-5-(1-hydroxyethyl)-1,3-dioxane was obtained as a cream solid (1.5 g.)